Synthesis, biologic properties, and molecular modeling studies of bis-indole based thiosemicarbazones

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dc.contributor.authorCeyhan, Sadik M.
dc.contributor.authorBingul, Murat
dc.contributor.authorSahin, Hasan
dc.contributor.authorBoga, Mehmet
dc.contributor.authorSaglam, Mehmet F.
dc.contributor.authorKandemir, Hakan
dc.contributor.authorSengul, Ibrahim F.
dc.date.accessioned2024-10-29T17:58:18Z
dc.date.available2024-10-29T17:58:18Z
dc.date.issued2024
dc.departmentTekirdağ Namık Kemal Üniversitesi
dc.description.abstractThe Schiff base condensation reaction of thiosemicarbazides and methylene bridged 2,2 '-bisindolylmethanes, prepared from the acid-catalyzed condensation of 3-aryl-4,6-dimethoxyindole-7-carbaldehydes and formaldehyde, produced a series of the targeted bis-indole based thiosemicarbazones. To explore the biological potential of the newly synthesized compounds, antidiabetic, anticholinesterase, and antioxidant activities were investigated. The structural derivatization carried out by the addition of bromophenyl ring at C3 position of the indole backbone increased the enzyme potency towards the anticholinesterase activity. Some of the targeted compounds showed selective the alpha-glucosidase enzyme inhibition activity. In addition to that, the inhibition concentrations were found to lower that the standard acarbose showing that they may be more efficient agents. Although most of the compounds were effective for the metal chelation capacities (CUPRAC), a couple of examples were found to be favorable for DPPH and ABTS assays. The presence of methyl substituted thiosemicarbazone tail with different indole back bones individually detected as promising targets for ABTS and DPPH activities. The compound methyl substituted thiosemicarbazone was also determined as the most potent agent with the 6 mu M inhibition concentration toward CUPRAC assay. Molecular docking study was performed to support the experimental results.
dc.description.sponsorshipResearch Found of the Gebze Technical University [2022-A105-44]
dc.description.sponsorshipThis work has been supported by Research Found of the Gebze Technical University (Project Number: 2022-A105-44).
dc.identifier.doi10.1007/s00706-024-03230-3
dc.identifier.endpage988
dc.identifier.issn0026-9247
dc.identifier.issn1434-4475
dc.identifier.issue10en_US
dc.identifier.scopus2-s2.0-85200002592
dc.identifier.scopusqualityQ3
dc.identifier.startpage977
dc.identifier.urihttps://doi.org/10.1007/s00706-024-03230-3
dc.identifier.urihttps://hdl.handle.net/20.500.11776/14210
dc.identifier.volume155
dc.identifier.wosWOS:001279189400001
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer Wien
dc.relation.ispartofMonatshefte Fur Chemie
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectHeterocycles
dc.subjectIndole
dc.subjectSchiff bases
dc.subjectBioorganic chemistry
dc.subjectAnticholinesterase
dc.subjectMolecular modelling
dc.titleSynthesis, biologic properties, and molecular modeling studies of bis-indole based thiosemicarbazones
dc.typeArticle

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